497236-40-5

Upstream product

• 125803-61-4 ethynylphenyl-iodonium-1,1,1-trifluoromethanesulfonate 
• 442155-91-1 4-methyl-N-{2-(phenylethynyl)phenyl}benzenesulfonamide 
• 615-43-0 2-iodophenylamine 
• 13141-38-3 2-phenylethynylaniline 
• 536-74-3 phenylacetylene 
• 133816-00-9 phenyl(trimethylsilylethynyl)iodonium triflate 
• 98-59-9 p-toluenesulfonyl chloride 
• 79-01-6 Trichloroethylene 

Downstream Products

• 1313483-70-3 1-phenyl-5-(toluene-4-sulfonyl)-5H-γ-carboline-3-carboxylic acid methyl ester 
• 1313483-60-1 C₂₆H₂₀N₂O₄S 

Relevant academic research and scientific papers

Strategies towards potent trypanocidal drugs: Application of Rh-catalyzed [2?+?2?+?2] cycloadditions, sulfonyl phthalide annulation and nitroalkene reactions for the synthesis of substituted quinones and their evaluation against Trypanosoma cruzi

Rhodium-catalyzed [2 + 2 + 2] cycloadditions, sulfonyl phthalide annulations and nitroalkene reactions have been employed for the synthesis of 56 quinone-based compounds. These were evaluated against Trypanosoma cruzi, the parasite that causes Chagas disease. The reactions described here are part of a program that aims to utilize modern, versatile and efficient synthetic methods for the one or two step preparation of trypanocidal compounds. We have identified 9 compounds with potent activity against the parasite; 3 of these were 30-fold more potent than benznidazole (Bz), a drug used for the treatment of Chagas disease. This article provides a comprehensive outline of reactions involving over 120 compounds aimed at the discovery of new quinone-based frameworks with activity against T. cruzi.

Rh-Catalyzed [2 + 2 + 2] Cycloadditions with Benzoquinones: De Novo Access to Naphthoquinones for Lignan and Type II Polyketide Synthesis

The first examples of Rh-catalyzed [2 + 2 + 2] cycloadditions between diynes and benzoquinones are described. The method enables de novo and step-economical access to challenging naphthoquinones that are of relevance to lignan and type II polyketide synthesis. The value of the chemistry is demonstrated by a short total synthesis of justicidone.

NaBArF4-Catalyzed Oxidative Cyclization of 1,5- and 1,6-Diynes: Efficient and Divergent Synthesis of Functionalized γ- and δ-Lactams

An efficient NaBArF4-catalyzed oxidative cyclization of readily available 1,5- and 1,6-diynes has been developed. Importantly, this transition metal-free oxidative catalysis proceeds via a presumable Lewis acid-catalyzed SN2’ pathway, which is distinct from the relevant oxidative rhodium and gold catalysis. This method leads to the facile and practical construction of a diverse range of synthetically useful γ- and δ-lactams in mostly good to excellent yields with broad substrate scope.

Gold(I)-Catalyzed Formal Intramolecular Dehydro-Diels-Alder Reaction of Ynamide-ynes: Synthesis of Functionalized Benzo[ b]carbazoles

A gold-catalyzed cycloisomerization of ynamide-ynes via a formal dehydro-Diels-Alder reaction has been developed, providing an attractive route to diversely substituted benzo[b]carbazoles. The reaction likely proceeds via regioselective attack of the pendant alkyne moiety to a keteniminium ion intermediate followed by benzannulation. The method offers several advantages such as high efficiency, mild reaction conditions, and wide functional group tolerance and serves as a highly useful complement to the thermal DDA reactions of ynamide-ynes.

Gold(I)-catalyzed 1,2-acyloxy migration/[3+2] cycloaddition of 1,6-diynes with an ynamide propargyl ester moiety: Highly efficient synthesis of functionalized cyclopenta[b]indoles

A gold-catalyzed cycloisomerization of 1,6-diynes containing an ynamide propargyl ester or carbonate moiety has been developed that provides an attractive route to a diverse-substituted 3-acyloxy-1,4-dihydrocyclopenta[b]indoles. Mechanistic studies indicate that the reaction likely proceeds through a competitive 1,2-OAc migration followed by [3+2] cycloaddition of the vinyl gold-carbenoid intermediate with the pendant triple bond. The synthetic utility of the obtained cyclopenta[b]indole products was demonstrated by their efficient transformations by deprotection or double-bond isomerization reactions.

Synthesis of carbazoles by dehydro Diels-Alder reactions of ynamides

A new approach to carbazoles and benzannulated carbazoles by means of intramolecular dehydro Diels-Alder of ynamides is reported. N-(o-Ethynyl)aryl ynamides and N-(o-ethynyl) arylynamides were prepared in a few steps starting from o-iodoaniline. Thermal c

Coupling and cycloaddition of ynamides: Homo- and Negishi coupling of tosylynamides and intramolecular [4 + 2] cycloaddition of N-(o-ethynyl)phenyl ynamides and arylynamides

N,N′-aryl- and N,N′-alkyl-buta-1,3-diyne-1,4-ditosylamides have been synthesized for the first time, in good to excellent yields, by copper-catalyzed dimerization of the corresponding N-aryl or N-alkyl tosylynamides. Negishi coupling of N-ethynylzinc tosy

Synthesis of carbazoles from ynamides by intramolecular dehydro Diels-Alder reactions

(Chemical Equation Presented) A new approach to carbazoles and benzannulated carbazoles by means of intramolecular dehydro Diels-Alder reactions of ynamides is reported. By using this approach, carbazoles and benzo[b]-, tetrahydrobenzo[b]-, naphtho[1,2-b]

A highly efficient and flexible synthesis of substituted carbazoles by rhodium-catalyzed inter- and intramolecular alkyne cyclotrimerizations

An A→ABC or A→ABCD ring-formation strategy proves extremely efficient for generating substituted carbazoles ([Eq. (1)]; Ts = tosyl). Inter- and intramolecular alkyne cyclotrimerizations mediated by Wilkinson's catalyst provide substituted carbazoles of re